AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2026 (see full year).
Return flights
| 10 Dec - 15 Dec | Delta | ||
| 12 Dec - 19 Dec | Delta | ||
| 20 Dec - 26 Dec | Delta | ||
| 19 Dec - 26 Dec | Delta | ||
| 19 Dec - 27 Dec | Delta |
Also check the deals for one-way flights from Chicago to San Juan in December.
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